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Kingston Penitentiary’s storied history full of notorious inmates, riots, escapes

When the Kingston Penitentiary first opened its doors in 1835, inmates were not allowed to speak, nod or even glance at each other.

It must have been quiet, then, within the prison’s ominous limestone confines. It is difficult to imagine that early silence, given the chaotic episodes that would follow.

Inmates getting ready for a Sunday baseball game in the exercise yard in August 1954 used cigarette lighters to set buildings on fire, beginning a riot that lasted only two hours but caused extensive damage to the penitentiary. (TORONTO STAR FILE PHOTO)

Tyrone "Ty" Conn escaped from the penitentiary in May 1999 and was on the lam for nearly two weeks before police tracked him down in Toronto.

A new hush falls over the 178-year-old institution this week as the pen ends its storied run as home to Canada’s most notorious criminals.

The federal government is shutting down the maximum-security facility as a cost-saving measure. Paul Bernardo, Russell Williams and the lesser-known among the still-living killers, rapists and burglars will serve their sentences elsewhere.

No longer a prison, the lakeside compound will sit idle for awhile as the government sorts out what to do with it. A tourist attraction à la Alcatraz — the decommissioned prison in San Francisco Bay — seems a good bet, given the high demand for tickets to a series of sold-out penitentiary tours set to run in October as a fundraiser for the United Way.

Those who enter the pen will wander the site of daring escapes, brutal beatings and savage riots.

“If walls could talk,” historian J. A. Edmison wrote in 1954, “we would indeed have a story of drama, of tragedy, of cruelty, of every vicissitude of human emotion. We would have a story of people who have been forever crushed in that penal environment and others who have found themselves in it.”

Empty of prisoners, yes, but the pen’s stories remain embedded in its foundation — those that have come to light, and many more that never will. As the prison closes, the Toronto Star delved into newspaper archives to bring you some of the most riveting tales of escape and revolt.

Great Escapes

Norman “Red” Ryan

One morning in September 1923, a few scheming prisoners lit a fire in the exercise yard to create a diversion. As smoke billowed across the grounds, they leaned a makeshift ladder against the wall and began to climb over.

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Red Ryan, a 28-year-old burglar, stood watch with a pitchfork as four accomplices made it to the other side. When a guard attempted to thwart the escape, Ryan impaled him and took off.

The following day, a novice Toronto Daily Star reporter, his first day on the job, was sent by train to Kingston. His name was Ernest Hemingway. In his 2,600-word report, Hemingway described Ryan as a “thick, freckle-faced man whose prison cap could not hide his flaming head.”

After the escape, Ryan robbed a Toronto bank and then made off to the United States, where was dubbed the “Jesse James of Canada.” After nearly a year on the lam, he was caught while picking up his mail at a post office in Minneapolis and sent back to Kingston to face 30 lashes and life in prison.

Changing gears, Ryan became a model prisoner — “Famous Bandit Proves Tender Nurse in Prison,” read one headline — and escaped Kingston again, this time by convincing Prime Minister R.B. Bennett to visit him in prison, then charming his way out.

“I was greatly impressed,” the politician later wrote of their 1934 meeting.

Freed the following year on Canada’s ticket-of-leave system, a precursor to parole, Ryan became the poster boy for prison reform.Hehosted a radio show, wrote a series of crime-doesn’t-pay articles for the Star and counted among his friends and acquaintances an archbishop, a senator and a top officer of the Salvation Army.

Meanwhile, however, Ryan was robbing banks in disguise.

On May 23, 1936, his double life caught up with him. Ryan, an accomplice and a police officer were killed in a gunfight during a holdup at a liquor store in Sarnia. The headline that ran with a Star story was unforgiving: “Ryan, Stupid, Callous, Goes to his Death Bungler and Coward.”

Tyrone “Ty” Conn

Just after lunch on May 6, 1999, a bank robber stuffed a dummy in his prison cell bed and went off to work at the pen’s canvas repair shop. On his calendar, Ty Conn had written “fishing trip 99.”

When the other canvas workers returned to their cells later that day, the 32-year-old hid under a pile of Canada Post mailbags and waited. Sometime in the evening, he assembled his tools: a ladder with a homemade extension, a steel hook and a 12-metre strip of canvas he would use as a rope.

It was after 11 p.m. when Conn broke through a locked screen door in the canvas shop’s loading bay and made a dash through the exercise yard to the wall. He had waited until the southeast tower guard went off duty, choosing a route guards in the other three towers couldn’t see. Conn sprinkled cayenne pepper along his path to mask his scent from the dogs. He went unnoticed on the security cameras and climbed easily over the 10-metre wall.

He made it to his mother’s apartment in Belleville, 75 kilometres away, before anyone even realized he was missing. It was 7:30 a.m. by the time a corrections employee noticed a rope hanging over the wall and sounded the alarm. It was the first successful escape in four decades.

Conn, who had robbed his first bank at age 16, was serving 37 years for a string of armed burglaries and property offences, as well as two previous escapes from other prisons. He was on Kingston’s list of prisoners most likely to make a run for it. “I’m beginning to think he has one motive in life, and that’s to escape from prison,” John Oddie, assistant warden at the time, said after the breakout.

The escape was instantly romanticized. The story dominated radio and television broadcasts and was splashed all over the front pages of newspapers for weeks. Many people felt bad for Conn, who had a terrible upbringing.

“Come on, be honest,” an editorial in the Kingston Whig-Standard began. “Part of you is cheering for Tyrone Conn.”

The convict was on the run for nearly two weeks before police tracked him down in the basement apartment of a home on Alberta Ave. in Toronto. He was on a cellphone speaking with a CBC producer when a gunshot rang out from the apartment and the line went dead. Whether by accident or on purpose, the escape artist killed himself.

Riots

Oct. 17, 1932

The first major riot in the prison’s history lasted six days, and came the year afterTim Buck, general secretary of the Communist Party of Canada, landed at the penitentiary on a conviction of “communist agitation.”

Naturally, early reports suggested Buck was to blame for the riots, and questioned whether a “communist uprising” was taking place. Turned out the problem was the cigarettes.

“Standing above every other grievance,” Arthur C. Carty wrote for the newspaper on Oct. 22, “is the question of cigarette papers, and the endless round of troubles growing out of forbidden uses of tobacco.”

Other concerns raised by inmates included favouritism or “small fry” treatment, a feeling of “dishonesty in high places” and the brutality of certain prison guards, Carty noted in his report.

Several shots were fired into the communist leader’s cell during the disturbance, but the government denied there was an assassination attempt against Buck.

The riot ended without casualties and led to calls for prison reform. Two decades would pass before the next major disturbance.

Aug. 15, 1954

Inmates were getting ready for a Sunday baseball game in the exercise yard when a group of them charged at the prison guards and used cigarette lighters to set buildings on fire, according to a front-page report in the Star.

It lasted only two hours, but caused extensive damage and panic. One guard, held hostage in the blacksmith shop, managed to escape by dressing in prisoner’s garb and mingling with the inmates. With flames visible from the downtown market square, worried wives of prison guards gathered in the street outside the penitentiary. In an attempt to calm things down, warden Walter Johnstone mounted the wall and stood facing the street, a cloud of dark smoke hanging in the air around him.

“Don’t worry,” he shouted above the roar of the flames, “your husbands are safe!”

The army and RCMP were called in to help quell the uprising, which involved 900 inmates. There were no casualties, but the estimated cost of damages at the time was $2 million.

April 14, 1971

For four days, inmates held six guards hostage and went to work destroying most of the cellblocks. The army was called in to help restore control. It was the most brutal, by far, of the three riots.

On the final night, 14 prisoners considered “undesirables” — mostly sex offenders — were tied to chairs in the centre of the dome, a circular hall linking the prison’s four main wings. The area had been turned into something like a “Roman circus,” a coroner who interviewed victims told the Star. The “undesirables” were covered in bed sheets and beaten with metal bars while hundreds watched over the rails from each of the prison’s four levels.

When the inmates surrendered the next morning, police were warned there could be up to 15 bodies, and extra coroners were called in from Toronto. In the end, only two prisoners died and all six guards escaped unharmed. A prisoner named Barrie MacKenzie was credited with risking his life for the release of the guards.

Inmates were granted no concessions, but an inquiry into the cause of the violent uprising ultimately led to them having some concerns remedied. It was, and will now remain, the penitentiary’s last riot.

With files from Toronto Star archives and The Canadian Press

Other notorious inmates

Roger “Mad Dog” Caron

During his 24 years behind bars, Caron is said to have made more escapes than any other convict in Canada. The bank-robbing author’s 1978 prison memoir, Go-Boy! Memories of a Life Behind Bars, was published the year he was paroled. He wrote three more books and was later rearrested on further robbery charges. In 2005, he was acquitted on five counts, including one accusation that he burgled a Loblaws, which Caron considered a slight to his reputation. He died April 11, 2012.

Clifford Olson

The British Columbia serial killer pleaded guilty in 1982 to first-degree murder in the slayings of 11 children and teens. He was later transferred from a Vancouver correctional centre to Kingston, where he spent years in isolation. Olson died of cancer two years ago in a Quebec prison. He was 71.

Wayne Boden

Known as the “vampire rapist,” Boden sexually assaulted and murdered four women in Montreal and Calgary between 1969 and 1971, leaving bite marks on his victims’ breasts. The serial killer died of acute skin cancer at Kingston in 2004.

Michael Briere

Briere is serving a life sentence for the 2003 murder of Toronto’s Holly Jones, a 10-year-old girl he abducted, strangled, sexually assaulted and dismembered. The killer was taken to Kingston after pleading guilty to the crime in 2004.

Paul Bernardo

From the late 1980s to the early 90s, Bernardo raped more than a dozen young women, most of them in Scarborough. In 1995, the schoolgirl killer and serial rapist was convicted in the kidnapping, rape and murder of Kristen French, 15, and Leslie Mahaffy, 14. His wife, Karla Homolka, served a 12-year term for manslaughter. Bernardo was sentenced to life and locked up in a Kingston pen cell the size of a walk-in closet.

Russell Williams

The former commander of CFB Trenton, an air force colonel, pleaded guilty in 2010 to the sexual slayings of Marie-France Comeau, 37, and Jessica Lloyd, 27, as well as a series of other sexual assaults and fetish burglaries. He and Bernardo were both held in a segregated section at Kingston, away from the other inmates.

Source: Toronto Star archives, Toronto Star library with files from The Canadian Press

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